The Way It Goes
by jaasminn
Summary: A collection of instances in the relationship that is Jeff and Annie.
1. Chapter 1

This isn't the first time I've ever written fanfiction; but it is the first time I've ever posted. Hope you enjoy!

* * *

Jeff walks into The Ballroom (because the hipsters found L Street) and starts looking around for someone to use the famous Winger charm on. He glances over to the pillar covered in polaroids next to the entrance where a tall, leggy redhead in a short red dress is standing. He walks toward her when he sees someone familiar sitting at the bar. It's Annie. She's drinking a screwdriver and resting her head on the counter. He's not sure why but he changes his mind and goes to the bar instead.

"Annie?" She turns to him and her eyes are red and puffy and he knows she's been crying.

She quickly wipes away the moisture from her eyes and replies "Jeff!" while very obviously forcing a smile. "What are you doing here?"

"Um, getting a drink... Are you okay?" He's not sure why she's crying but he knows it's not something he did because it's Saturday and they didn't have school.

"Yeah, of course." She knows what she said isn't convincing but hopes he'll let it go.

He doesn't. "Are you sure because you don't look so good."

"Thanks."

"You know what I meant."

She sighs and confesses, "Dave and I broke up."

Dave was the new guy Annie had been dating. He was tall, but not too tall for Annie and he had light brown hair that always looked perfect without product (so he said) and he dressed nicely and no Jeff was not jealous of him... Even though Britta said he was more attractive him, which he wasn't. But Annie swooned every time he looked at her (which was often) and they were dating a week later.

"Oh.. Why?"

"He kissed another girl."

Jeff clenched his fists. "He did what?!"

"Jeff, it wasn't big deal." she took another sip of her drink before continuing. "She kissed him and he apologized and said he didn't want her."

Jeff was confused at this, "Then, why did you guys break up?" Wait, what did he just say?

She looked down and started to play with the hem of her dress. "The way he looked at her."

"Huh?"

"I broke up with him because I saw the way he looked at her." She paused. "It was the way no one's ever looked at me before."

Jeff felt his heart sink. He wasn't really sure how to respond to that but her eyes started watering and his brain kicked in. "Annie you're one of the most caring people I have ever met and you'll find someone better."

She sniffled as a small smile pulled at her lips. "You're just saying that to be nice."

"Do you remember that day when Troy and Abed had that pillows versus blankets war?"

She furrowed her brow. "Yeah," she said slowly. "Why?"

He let out a breath, feeling embarassed over what he was going to say. "Well, you were the one who convinced me to help Troy and Abed."

Her face lit up immediately. "Really? Aw, Jeff!"

"Yeah, yeah okay don't get too excited."

She already was. A smile was plastered on her face. Annie got up and gave him a tight hug. She knew the redhead that had been looking at Jeff all night was glaring at her but she didn't really care. When they broke apart she said, "Well I should be going home now. Troy and Abed aren't going to cook for themselves."

"Are you sure you're okay? Do you want me to go with you?"

"No it's okay. Plus," she said nodding her head in the direction of the girl in the red dress, "I would hate to be the one to take you away from all of your fans," stepping closer she says, "but thank you" before getting on her tip toes and placing a small kiss on his cheek. "for being the only person to make me smile all day."

He watches her leave and can't help but be upset that she encouraged him to go home with the other girl. As she walks out of the bar she looks back at him. He's walking over to the bimbo and she can't help but be upset and confused that she didn't say yes when he offered to go home with her.


	2. Chapter 2

Later that night Jeff is laying in bed, unsure of why he can't sleep. Alicia, wait, Alyssa?, Amelia? He can't remember her name. Tight dress redhead left over an hour ago. He's staring up at the ceiling. He should be asleep, but he can't. For some reason he feels guilty. Like he shouldn't have slept with that woman. It didn't make sense. He just needed more vitamins. Yeah, that's it.

* * *

Jeff is staring at his last test grade. Crap. He cannot afford to fail a class right now. Not when he's so close to graduating. He hates the fact that this doesn't come easy to him and he has to study. He leaves class and see's his solution walking past him.

"Annie!"

She turns and smiles, "Hey Jeff."

"I need your help."

Her smile widens. "With what?"

"I'm kinda sorta failing a class."

"You're what?! Jeff, why didn't you study if you knew you were going to", She pauses to lower her voice. "fail?"

"Annie will you help me or not?" He says, sounding annoyed.

"Alright. When do you want to meet up? After school in the study room tomorrow works for me."

"I can't do it tomorrow. I have a guy coming over to fix my cable, but if you want you can come over after he leaves."

"You want me to go to your apartment?"

"Is that okay with you?"

"Of course." She says nervously, "There's no reason why it wouldn't be."

He lets out a small laugh, "I'll see you tomorrow."


	3. Chapter 3

Annie is staring at the door. She reaches into her bag to retrieve a small piece of paper that has the numbers 204 carefully written on it. Annie knows that she's at the right apartment, but she's a little afraid to go in. She doesn't know why because they've been friends for over three years and he was the one who asked her to come over. Usually she wouldn't be so nervous, but this was different. She was going to be at Jeff Winger's apartment. It was going to be just the two of them... at his apartment. Not that she still has feelings for him or anything because she doesn't, but a part of her just can't shake him from her system. She finally decides she's ready and knocks the door.

"Annie."

"Jeff!" She knows what she says is coming out a bit too enthusiastic but she hopes he'll shrug it off. "Do you have all your books? because if you don't I have mine."

He smiles at the fact that she's so excited to study. She walks in and looks around. It's a lot like she thought it would. There's a nice tv and weights on the floor by a shelf with some books, three RC cars and some other miscellaneous things. She thinks back to when he and Troy were completely obsessed with racing their toy cars. It seems like so long ago. Annie walks past the couches to get to the dining area. When she does, she sets all of her stuff on the black table and looks up to see a Monaco poster. Annie smiles to herself because of course he has one. There's a painting of a dancer next to it. She turns around at see's another painting by the tv that's drawn in the same style.

"Where did you get these paintings? They're beautiful."

"My mom likes to paint." He lets out a small chuckle. "She likes to send me these sometimes around the time of my birthday."

Annie starts doing that thing where her face melts and Jeff knows what's coming up next. "Aw, Jeff! Thats so sweet!"

"Annie, they're just paintings."

She pulls out one of the speckled grey chairs and sits in it before grabbing her backpack and pulling out a light blue binder. She opens it to pull out her notes and says, "You're a big softie." before gesturing to the seat next to her

Jeff feels a small smile pull at his lips. He sits in the seat and says, "Should we get started?"

* * *

Twenty minutes later Annie is regretting her decision to have Jeff sit by her. She can smell his cologne.

Jeff pinches the bridge of his nose, "Ugh, Annie can we take a break?"

"Jeff, You can't just take a break every time you get a stress headache."

He gets up and walks over to the small shelf of food. He grabs a box of Cheez-Its and puts it on the table. "You want some?"

Annie's a little confused because she never would have thought Jeff ate any form of junk food. "Um, okay... but why do you have those? You never eat carbs."

"Chang made me buy them when he lived here." He shuddered at the thought. "I'd rather not talk about him."

"Okay, well we should talk about this assign-" She was quickly interrupted by a loud exasperated Ugh. He moved to the kitchen to grab a bottle of scotch. Jeff grabs a glass from his cabinet when he gets interrupted.

"Jeff, what are you doing?"

"Getting a drink."

"In that?" she says motioning to the glass he's holding.

He looks at her confused. "Um, Yes?"

Annie gets up and opens one of his cabinets to pull out a small nosing glass. She takes the bottle of scotch from him and pours a small amount into the glass. She takes the glass and swirls the scotch around before dumping it in the sink.

"Annie, what are you doing?" He says in a confused voice.

"I'm getting rid of impurities in the cup." She pours more scotch into the glass and grabs a cup of water.

He looks back at her with an impressed expression on his face. "Since when do you know so much about scotch?"

Annie sticks her finger in the water to test it before pouring a small amount into the glass. "I watched my dad do this all the time when I was younger. I used to research this kind of stuff because I thought it would impress him." She looks down feeling embarrased. "It's stupid, I know."

He cups her face so she's looking at him. "Annie, that's not stupid." Jeff drops his hand and pauses because he knows what he is going to say next will make Annie give him that look of pity that he always got from anyone who knew about his situation. "I used to sneak behind the counters at stores to steal boxes of cigarettes, so my dad wouldn't have to leave the house to buy them."

There's a pause as she looks at him. It's not a look of pity or sadness. Annie is looking at him with concern. Like she truly cares about him. It's a look so genuine, Jeff is taken aback. It's a look he's never experienced before. He feels this pull towards Annie because they're so different, yet they've had very similar encounters in their lives and he doesn't really know what to say to her so he doesn't say anything.

Instead he pulls her face towards his closing the space between them. He kisses her and it's slow at first, but it grows in intensity when Jeff moves his arm down to her waist to pull her closer. Annie feels herself melt into him and it's been so long and the kiss becomes desperate as she clings to him. Finally, she pulls away for air. Annie looks up at Jeff. He looks.. nervous. She smiles at this because Jeff Winger does not get nervous especially around women. This thought gives her the confidence to release herself from his grip and pull him towards the bedroom.


	4. Chapter 4

Jeff wakes up holding Annie. He looks down at her sleeping. Carefully, he pushes her hair off of her face. Jeff can't help but smile because holy crap he really likes this girl. He's a little unsure of how she is going to react in the morning but he doesn't really care right now because he's happy. With that in mind he lays his head back down on the pillow and slowly falls asleep

* * *

The next morning Annie wakes up with Jeff's arms wrapped around her. She feels a smile pull at her lips because of the way he looks when he sleeps; but it fades quickly when she realizes what happened the night before. She had sex with Jeff. Crap. She felt a rush of panic jolt through her. What would he say when he got up? Would he tell her to leave? Would he let her stay? Crap. Crap, crap, crap. Why did she do that?... and why was she thinking like Abed? Annie took a deep breath. Maybe he would be okay with what happened. They had grown closer this year. Maybe he would want more...

She coincidentally chose that moment to think back to their second year at Greendale. Annie, I think you're reading into some things. He wouldn't want more. She sighed. Slowly, Annie releases herself from his embrace and gets out of the bed. She grabs her clothes to get dressed when she sees Jeff's shirt on the floor. Annie takes it and places it on a wooden hanger. She buttons it up so it sits nicely. She knows how Jeff gets about his clothes. She looks back at him. He's sleeping soundly just as before. Annie feels her eyes water just a little, before getting dressed and leaving his apartment.

* * *

A week after the "incident" Jeff walks into his therapist, Dr. Hopkins', office for his session. He's confused as to what happened the other night with Annie. He sits on the couch not really sure what to say (even though he has a thousand things on his mind). He's avoids all eye contact with the doctor.

"Mr. Winger is there something you'd like to tell me?"

"What?" He pauses, not really sure whether to tell him or not. "Nope. Just coming for my daily session."

"Is this about Annie?"

"What?" How the hell did he know? "Wait, how— I mean, what are you talking about?" He tries to say it as nonchalantly as possible.

Apparently it really isn't working because Dr. Hopkins replies, "I know it's about her."

"How?"

"I have my ways."

Jeff sits there confused at what his therapist is saying.

"Would you like to tell me what happened?"

"We slept together." The words sound so dumb coming out of his mouth. He's freaking out about having sex when he's done it a hundred times before.

There's a pause. It's weird and uncomfortable because, being Jeff Winger, awkward pauses don't usually happen. "How was it?"

"What?" He furrows his brow thinking he didn't hear him right. "Are you really asking me how the sex was?"

"Yes, how was it?"

Jeff shifted uncomfortably, not exactly sure how to respond. "Good, I guess."

"Just good?" Dr. Hopkins paused to write something on his notepad, "Wasn't anything special?"

"No. It was... I just—" He's not really sure how to continue. His brain is still reeling from everything that happened.

"How did it make you feel?"

"Okay, did you seriously just ask me how sex feels? What kind of doctor are you?"

"No I'm asking you how Annie made you feel."

He pauses. "I don't know. I guess she— I mean it was— ugh." He doesn't exactly know what to say. That night she made him feel great (obviously), but not just from the sex. She made him feel like he was more than just a piece of very, very handsome meat. The way she looked at him during... well you know.. It was like he really meant something to her. God, he sounded cheesy.

"Where is she now?"

"Annie? At her apartment. I think. I'm not really sure." He sighed and layed on the couch, "She left before I could wake up."

"Do we need to talk about your father now?"

He pinched the bridge of his nose before sitting up.

Dr. Hopkins could see this was a lot to handle so he decided to hold back a little on the dad stuff. Instead he said, "If you had woken up with Annie, would you have left?"

Jeff immediately answers, "No! I mean, maybe. I— I don't know." Jeff felt something strange wash over him. Anger? Confusion? He wasn't really sure. Yes they were closer now and she was one of his best friends, but a part of him couldn't stop thinking about how he'd freak out and leave and how it would hurt her or how he would get insecure about the age difference.

"What exactly do you want from Annie?"

"What do you mean?"

"Do you want to just be friends or do you want a relationship? Is she just another casual sex partner for you?"

Honestly, Jeff wasn't sure what he wanted with Annie. She was not a casual sex partner. He had feelings for her, but would it work out? Would he end up hurting her? Or would she hurt him.. No. Not thinking about that.

"Mr. Winger, until you find out what you want with her this problem will not be solved." Dr. Hopkins looked over at the clock and saw that time was up. "I'll see you next week"

He got up and simply said, "Okay." before walking out the door.

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Sorry it took so long to update! I've been tinkering with this chapter for a while and I'm not so sure about it. Thanks for all the kind reviews by the way! I really appreciate them :)


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